SE439439B - Katalysator och hydroformyleringsforfarande - Google Patents
Katalysator och hydroformyleringsforfarandeInfo
- Publication number
- SE439439B SE439439B SE8007080A SE8007080A SE439439B SE 439439 B SE439439 B SE 439439B SE 8007080 A SE8007080 A SE 8007080A SE 8007080 A SE8007080 A SE 8007080A SE 439439 B SE439439 B SE 439439B
- Authority
- SE
- Sweden
- Prior art keywords
- rhodium
- ligand
- catalyst
- complex
- hydroformylation
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 217
- 238000000034 method Methods 0.000 title claims abstract description 136
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 152
- 230000008569 process Effects 0.000 claims abstract description 110
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 169
- 230000015572 biosynthetic process Effects 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011435 rock Substances 0.000 claims description 2
- 239000003446 ligand Substances 0.000 abstract description 228
- 239000010948 rhodium Substances 0.000 abstract description 135
- 229910052703 rhodium Inorganic materials 0.000 abstract description 102
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract description 87
- 239000011541 reaction mixture Substances 0.000 abstract description 52
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 41
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 35
- 230000036961 partial effect Effects 0.000 abstract description 28
- 229910052799 carbon Inorganic materials 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 179
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 108
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 101
- 239000000047 product Substances 0.000 description 94
- 239000000203 mixture Substances 0.000 description 79
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 72
- 150000001299 aldehydes Chemical class 0.000 description 71
- 238000002474 experimental method Methods 0.000 description 68
- 150000001336 alkenes Chemical class 0.000 description 63
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 60
- 230000001965 increasing effect Effects 0.000 description 58
- 239000007789 gas Substances 0.000 description 46
- -1 Canadian Patent 1 Chemical compound 0.000 description 43
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 40
- 239000007788 liquid Substances 0.000 description 38
- 230000000694 effects Effects 0.000 description 37
- 235000019256 formaldehyde Nutrition 0.000 description 37
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 36
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 34
- 239000000376 reactant Substances 0.000 description 30
- 238000007792 addition Methods 0.000 description 29
- 238000005984 hydrogenation reaction Methods 0.000 description 28
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 27
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical class C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 27
- NQQJIBHSTRRTIU-UHFFFAOYSA-N diphenyl(2-trimethylsilylethyl)phosphane Chemical compound C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1 NQQJIBHSTRRTIU-UHFFFAOYSA-N 0.000 description 23
- 150000003003 phosphines Chemical class 0.000 description 23
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 21
- 239000006227 byproduct Substances 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 230000006399 behavior Effects 0.000 description 17
- 230000003197 catalytic effect Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 238000010924 continuous production Methods 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- 238000006317 isomerization reaction Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- 238000005810 carbonylation reaction Methods 0.000 description 12
- 230000008859 change Effects 0.000 description 12
- 238000001030 gas--liquid chromatography Methods 0.000 description 12
- 239000011574 phosphorus Substances 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 description 11
- 230000003247 decreasing effect Effects 0.000 description 11
- 150000003283 rhodium Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000006315 carbonylation Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000013638 trimer Substances 0.000 description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000006555 catalytic reaction Methods 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- 238000006073 displacement reaction Methods 0.000 description 9
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 9
- 230000007246 mechanism Effects 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- 238000007086 side reaction Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- RMLOZYVMENRVSS-UHFFFAOYSA-N formaldehyde;rhodium Chemical class [Rh].O=C RMLOZYVMENRVSS-UHFFFAOYSA-N 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 7
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000004508 fractional distillation Methods 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 6
- 125000002348 vinylic group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000009918 complex formation Effects 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 5
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical class P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- NLSOYYPJGJBGRT-UHFFFAOYSA-N 2,2-dimethylpropyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC(C)(C)C)C1=CC=CC=C1 NLSOYYPJGJBGRT-UHFFFAOYSA-N 0.000 description 4
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
- CHUBDMDLPFIHPY-UHFFFAOYSA-N 3,3-dimethylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC(C)(C)C)C1=CC=CC=C1 CHUBDMDLPFIHPY-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001133 acceleration Effects 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 238000005882 aldol condensation reaction Methods 0.000 description 4
- 125000000746 allylic group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- NNLYMENHIVUOLT-UHFFFAOYSA-N diphenyl(2-phenylethyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCC1=CC=CC=C1 NNLYMENHIVUOLT-UHFFFAOYSA-N 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- UCEAMHUPTPYISC-UHFFFAOYSA-N phosphane rhodium Chemical class P.P.P.[Rh] UCEAMHUPTPYISC-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 3
- FEYKDRUEISVYSY-UHFFFAOYSA-N 2-[2-diphenylphosphanylethyl(dimethyl)silyl]ethyl-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[Si](C)(C)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 FEYKDRUEISVYSY-UHFFFAOYSA-N 0.000 description 3
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 3
- HIYCYWYGFFFCKU-UHFFFAOYSA-N 2-ethylsulfonylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCS(=O)(=O)CC)C1=CC=CC=C1 HIYCYWYGFFFCKU-UHFFFAOYSA-N 0.000 description 3
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 3
- 241001446467 Mama Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IIHWUHQYPQSWRK-UHFFFAOYSA-N diphenyl(2-triphenylsilylethyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IIHWUHQYPQSWRK-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- GTBGHTLFBQMXTN-UHFFFAOYSA-N ethenyl(tripropyl)silane Chemical compound CCC[Si](CCC)(CCC)C=C GTBGHTLFBQMXTN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XZMMPTVWHALBLT-UHFFFAOYSA-N formaldehyde;rhodium;triphenylphosphane Chemical compound [Rh].O=C.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XZMMPTVWHALBLT-UHFFFAOYSA-N 0.000 description 3
- 229910000856 hastalloy Inorganic materials 0.000 description 3
- WHNGQRQJGDUZPJ-UHFFFAOYSA-N hexyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCC)C1=CC=CC=C1 WHNGQRQJGDUZPJ-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000007342 radical addition reaction Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 238000007725 thermal activation Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical group CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 2
- WJHOKLFZQVKFJP-UHFFFAOYSA-N 3-(3-diphenylphosphanylpropoxy)propyl-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCOCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 WJHOKLFZQVKFJP-UHFFFAOYSA-N 0.000 description 2
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 2
- RQYBVDYQLYEESF-UHFFFAOYSA-N 3-methylsulfanylpropyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCSC)C1=CC=CC=C1 RQYBVDYQLYEESF-UHFFFAOYSA-N 0.000 description 2
- PKYIOXGHYZJCRH-UHFFFAOYSA-N 3-phosphanylpropylphosphane Chemical compound PCCCP PKYIOXGHYZJCRH-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QZUPHAGRBBOLTB-UHFFFAOYSA-N NSC 244302 Chemical compound C=1C=CC=CC=1P(C(C)(C)C)C1=CC=CC=C1 QZUPHAGRBBOLTB-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004873 anchoring Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- UZCPNEBHTFYJNY-UHFFFAOYSA-N benzyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 UZCPNEBHTFYJNY-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 230000001687 destabilization Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- RPYUWYHQEDMHLE-UHFFFAOYSA-N diphenyl(2-trimethylsilylethyl)phosphane formaldehyde rhodium Chemical class [Rh].O=C.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1 RPYUWYHQEDMHLE-UHFFFAOYSA-N 0.000 description 2
- KAEFQSPOQYVUGU-UHFFFAOYSA-N diphenyl(2-trimethylsilylethyl)phosphane rhodium Chemical class [Rh].C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1 KAEFQSPOQYVUGU-UHFFFAOYSA-N 0.000 description 2
- IRYNKYCSPDVWKJ-UHFFFAOYSA-N diphenyl(2-tripropylsilylethyl)phosphane Chemical compound C=1C=CC=CC=1P(CC[Si](CCC)(CCC)CCC)C1=CC=CC=C1 IRYNKYCSPDVWKJ-UHFFFAOYSA-N 0.000 description 2
- UPQYNEYVDRPMPX-UHFFFAOYSA-N diphenyl(trimethylsilylmethyl)phosphane Chemical compound C=1C=CC=CC=1P(C[Si](C)(C)C)C1=CC=CC=C1 UPQYNEYVDRPMPX-UHFFFAOYSA-N 0.000 description 2
- AJVBXLXLODZUME-UHFFFAOYSA-N ethenyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=C)C1=CC=CC=C1 AJVBXLXLODZUME-UHFFFAOYSA-N 0.000 description 2
- OVOIHGSHJGMSMZ-UHFFFAOYSA-N ethenyl(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=C)C1=CC=CC=C1 OVOIHGSHJGMSMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HCZDSQSBFCVXFG-UHFFFAOYSA-N methyl 3-diphenylphosphanylpropanoate Chemical compound C=1C=CC=CC=1P(CCC(=O)OC)C1=CC=CC=C1 HCZDSQSBFCVXFG-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- UIZVMOZAXAMASY-UHFFFAOYSA-N vinyl butanol Natural products OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- KEMUGHMYINTXKW-NQOXHWNZSA-N (1z,5z)-cyclododeca-1,5-diene Chemical compound C1CCC\C=C/CC\C=C/CC1 KEMUGHMYINTXKW-NQOXHWNZSA-N 0.000 description 1
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 description 1
- SPEMAJUUXYFGDZ-UHFFFAOYSA-N 1-(2-diphenylphosphanylethyl)pyrrolidin-2-one Chemical compound O=C1CCCN1CCP(C=1C=CC=CC=1)C1=CC=CC=C1 SPEMAJUUXYFGDZ-UHFFFAOYSA-N 0.000 description 1
- DKWVLFXGDTZKHN-UHFFFAOYSA-N 1-diphenylphosphanyl-n,n-diethylpropan-2-amine Chemical compound C=1C=CC=CC=1P(CC(C)N(CC)CC)C1=CC=CC=C1 DKWVLFXGDTZKHN-UHFFFAOYSA-N 0.000 description 1
- BJEWLOAZFAGNPE-UHFFFAOYSA-N 1-ethenylsulfonylethane Chemical compound CCS(=O)(=O)C=C BJEWLOAZFAGNPE-UHFFFAOYSA-N 0.000 description 1
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- APWRLAZEMYLHKZ-UHFFFAOYSA-N 2-amino-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1C APWRLAZEMYLHKZ-UHFFFAOYSA-N 0.000 description 1
- JCAUAUKUBUBNSB-UHFFFAOYSA-N 2-diphenylphosphorylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 JCAUAUKUBUBNSB-UHFFFAOYSA-N 0.000 description 1
- QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical compound C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 description 1
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- ZAFAFECQYDAMLA-UHFFFAOYSA-N 2-methylpentanal 3-methylpentanal Chemical compound CCCC(C)C=O.CCC(C)CC=O ZAFAFECQYDAMLA-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- FWFZRPMNAAFGBA-UHFFFAOYSA-N 2-phosphanylethylphosphane Chemical compound PCCP FWFZRPMNAAFGBA-UHFFFAOYSA-N 0.000 description 1
- LSZBLDOVMWGWEH-UHFFFAOYSA-N 2-propylheptyl pentanoate Chemical compound CCCCCC(CCC)COC(=O)CCCC LSZBLDOVMWGWEH-UHFFFAOYSA-N 0.000 description 1
- MRXUZWNEOUZHKM-UHFFFAOYSA-N 2-trimethylsilylethylphosphane Chemical compound C[Si](C)(C)CCP MRXUZWNEOUZHKM-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- IIMYISDSPKQURV-UHFFFAOYSA-N 3,3-diphenylpropylsilane Chemical compound C1(=CC=CC=C1)C(CC[SiH3])C1=CC=CC=C1 IIMYISDSPKQURV-UHFFFAOYSA-N 0.000 description 1
- KXRBUSCGRAZWAB-UHFFFAOYSA-N 3-diphenylphosphanyl-n,n-diethylpropan-1-amine Chemical compound C=1C=CC=CC=1P(CCCN(CC)CC)C1=CC=CC=C1 KXRBUSCGRAZWAB-UHFFFAOYSA-N 0.000 description 1
- DQZWMOWSTWWMPP-UHFFFAOYSA-N 3-diphenylphosphanylpropan-1-amine Chemical compound C=1C=CC=CC=1P(CCCN)C1=CC=CC=C1 DQZWMOWSTWWMPP-UHFFFAOYSA-N 0.000 description 1
- WJSIEWJPUZANTB-UHFFFAOYSA-N 3-diphenylphosphanylpropan-1-ol Chemical compound C=1C=CC=CC=1P(CCCO)C1=CC=CC=C1 WJSIEWJPUZANTB-UHFFFAOYSA-N 0.000 description 1
- OTSIFUHGOBFOTH-UHFFFAOYSA-N 3-diphenylphosphanylpropanoic acid Chemical compound C=1C=CC=CC=1P(CCC(=O)O)C1=CC=CC=C1 OTSIFUHGOBFOTH-UHFFFAOYSA-N 0.000 description 1
- UCKDLPNTSZJFRJ-UHFFFAOYSA-N 3-diphenylphosphanylpropyl acetate Chemical compound C=1C=CC=CC=1P(CCCOC(=O)C)C1=CC=CC=C1 UCKDLPNTSZJFRJ-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 1
- UZGPHABYBQWSJL-UHFFFAOYSA-N 3-methylpentyl(diphenyl)phosphane Chemical compound C1(=CC=CC=C1)P(C1=CC=CC=C1)CCC(CC)C UZGPHABYBQWSJL-UHFFFAOYSA-N 0.000 description 1
- CHYGGFBYQYUTDS-UHFFFAOYSA-N 3-morpholin-4-ylpropyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCN1CCOCC1 CHYGGFBYQYUTDS-UHFFFAOYSA-N 0.000 description 1
- YGRVCNYIEKLRED-UHFFFAOYSA-N 4,4-diphenylbutylphosphane Chemical compound C=1C=CC=CC=1C(CCCP)C1=CC=CC=C1 YGRVCNYIEKLRED-UHFFFAOYSA-N 0.000 description 1
- JZTDMOXKKVDWRY-UHFFFAOYSA-N 4-chloro-2,2-dimethylhexane Chemical compound CCC(Cl)CC(C)(C)C JZTDMOXKKVDWRY-UHFFFAOYSA-N 0.000 description 1
- ZDDPOEGGLYVTNK-UHFFFAOYSA-N 4-diphenylphosphanylbutan-2-one Chemical compound C=1C=CC=CC=1P(CCC(=O)C)C1=CC=CC=C1 ZDDPOEGGLYVTNK-UHFFFAOYSA-N 0.000 description 1
- XJFFUXNWVUZUIF-UHFFFAOYSA-N 4-ethenylisoindole-1,3-dione Chemical compound C=CC1=CC=CC2=C1C(=O)NC2=O XJFFUXNWVUZUIF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- YSWZHLFDTWYPFA-UHFFFAOYSA-N 6-phosphanylhexylphosphane Chemical compound PCCCCCCP YSWZHLFDTWYPFA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- BBHPNOUAKXNQRW-UHFFFAOYSA-N C1(=CC=CC=C1)[Mg].Cl Chemical compound C1(=CC=CC=C1)[Mg].Cl BBHPNOUAKXNQRW-UHFFFAOYSA-N 0.000 description 1
- 101150026868 CHS1 gene Proteins 0.000 description 1
- OCJFIYBCHBNHQB-UHFFFAOYSA-N C[Si](C)(C)CCC1=C(C(=C(C=C1)PC1=CC=CC=C1)CC[Si](C)(C)C)CC[Si](C)(C)C Chemical compound C[Si](C)(C)CCC1=C(C(=C(C=C1)PC1=CC=CC=C1)CC[Si](C)(C)C)CC[Si](C)(C)C OCJFIYBCHBNHQB-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001071608 Erodium Species 0.000 description 1
- 101100461919 Homo sapiens OR51E1 gene Proteins 0.000 description 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 229910021407 M-carbon Inorganic materials 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- 101100457407 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) mmm-1 gene Proteins 0.000 description 1
- HYBBKUAYLJOAIQ-UHFFFAOYSA-N O=C.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical class O=C.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 HYBBKUAYLJOAIQ-UHFFFAOYSA-N 0.000 description 1
- 102100025127 Olfactory receptor 51E1 Human genes 0.000 description 1
- YITACKIRMYHUNY-UHFFFAOYSA-N P.P.[Rh].O=C Chemical class P.P.[Rh].O=C YITACKIRMYHUNY-UHFFFAOYSA-N 0.000 description 1
- GAYMWACCKNFSNA-UHFFFAOYSA-N P.[PH3]=O Chemical compound P.[PH3]=O GAYMWACCKNFSNA-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 238000006851 Roelen carbonylation reaction Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- CBXOEWNRYOSZTE-UHFFFAOYSA-N [Na].P Chemical class [Na].P CBXOEWNRYOSZTE-UHFFFAOYSA-N 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- AXMKEYXDFDKKIO-UHFFFAOYSA-N bilane Chemical compound C=1C=C(CC=2NC(CC=3NC=CC=3)=CC=2)NC=1CC1=CC=CN1 AXMKEYXDFDKKIO-UHFFFAOYSA-N 0.000 description 1
- USEVXHPKGVKJBF-UHFFFAOYSA-N bis(2,3-dimethylphenyl)-methylphosphane Chemical compound C=1C=CC(C)=C(C)C=1P(C)C1=CC=CC(C)=C1C USEVXHPKGVKJBF-UHFFFAOYSA-N 0.000 description 1
- VVIGJTLLPPTWRI-UHFFFAOYSA-N bis(4-methoxyphenyl)-propylphosphane Chemical compound C=1C=C(OC)C=CC=1P(CCC)C1=CC=C(OC)C=C1 VVIGJTLLPPTWRI-UHFFFAOYSA-N 0.000 description 1
- QRHCILLLMDEFSD-UHFFFAOYSA-N bis(ethenyl)-dimethylsilane Chemical compound C=C[Si](C)(C)C=C QRHCILLLMDEFSD-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- IEKXSSZASGLISC-UHFFFAOYSA-N but-3-enyl acetate Chemical compound CC(=O)OCCC=C IEKXSSZASGLISC-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ACTAPAGNZPZLEF-UHFFFAOYSA-N chloro(tripropyl)silane Chemical compound CCC[Si](Cl)(CCC)CCC ACTAPAGNZPZLEF-UHFFFAOYSA-N 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical class ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZXKWUYWWVSKKQZ-UHFFFAOYSA-N cyclohexyl(diphenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZXKWUYWWVSKKQZ-UHFFFAOYSA-N 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- DPFCRMGFCUKIJZ-UHFFFAOYSA-N difluoro(phenyl)phosphane Chemical compound FP(F)C1=CC=CC=C1 DPFCRMGFCUKIJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- FHBLAOOKRWZROM-UHFFFAOYSA-N diphenyl(2-phenylmethoxyethyl)phosphane Chemical compound C(C1=CC=CC=C1)OCCP(C1=CC=CC=C1)C1=CC=CC=C1 FHBLAOOKRWZROM-UHFFFAOYSA-N 0.000 description 1
- MNBMHLHGGQPICR-UHFFFAOYSA-N diphenyl(2-propoxyethyl)phosphane Chemical compound C=1C=CC=CC=1P(CCOCCC)C1=CC=CC=C1 MNBMHLHGGQPICR-UHFFFAOYSA-N 0.000 description 1
- FLTMFXMAEKTMCE-UHFFFAOYSA-N diphenyl(2-pyridin-2-ylethyl)phosphane formaldehyde rhodium Chemical compound [Rh].O=C.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCC1=CC=CC=N1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCC1=CC=CC=N1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCC1=CC=CC=N1 FLTMFXMAEKTMCE-UHFFFAOYSA-N 0.000 description 1
- XZYKUQHNUMYJNO-UHFFFAOYSA-N diphenyl(3-trimethylsilylpropyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC[Si](C)(C)C)C1=CC=CC=C1 XZYKUQHNUMYJNO-UHFFFAOYSA-N 0.000 description 1
- GIOIKQSTWVFMEW-UHFFFAOYSA-N diphenyl(dipropyl)silane Chemical compound C=1C=CC=CC=1[Si](CCC)(CCC)C1=CC=CC=C1 GIOIKQSTWVFMEW-UHFFFAOYSA-N 0.000 description 1
- CRFFOIRTXVBCST-UHFFFAOYSA-N diphenyl-[2,2,2-tris(trimethylsilyl)ethyl]phosphane Chemical compound C=1C=CC=CC=1P(CC([Si](C)(C)C)([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1 CRFFOIRTXVBCST-UHFFFAOYSA-N 0.000 description 1
- NKQIHPAFIPIAMJ-UHFFFAOYSA-N diphenyl-[2-[tris(2-diphenylphosphanylethyl)silyl]ethyl]phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[Si](CCP(C=1C=CC=CC=1)C=1C=CC=CC=1)(CCP(C=1C=CC=CC=1)C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 NKQIHPAFIPIAMJ-UHFFFAOYSA-N 0.000 description 1
- WMFHTIJCSNSMDO-UHFFFAOYSA-N diphenylphosphinoethyl-pss Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[Si](O1)(O2)O[Si](O3)(C4CCCC4)O[Si](O4)(C5CCCC5)O[Si]1(C1CCCC1)O[Si](O1)(C5CCCC5)O[Si]2(C2CCCC2)O[Si]3(C2CCCC2)O[Si]41C1CCCC1 WMFHTIJCSNSMDO-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000003041 laboratory chemical Substances 0.000 description 1
- 239000013541 low molecular weight contaminant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- XFARCVVMIMKPGK-UHFFFAOYSA-N methyl-phenyl-(2-trimethylsilylphenyl)phosphane Chemical compound C[Si](C)(C)C1=C(C=CC=C1)P(C1=CC=CC=C1)C XFARCVVMIMKPGK-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JWAJUTZQGZBKFS-UHFFFAOYSA-N n,n-diethylprop-2-en-1-amine Chemical compound CCN(CC)CC=C JWAJUTZQGZBKFS-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 238000005887 phenylation reaction Methods 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- RDHJHIVIEXVZFX-UHFFFAOYSA-N phosphane;rhodium Chemical class P.P.[Rh] RDHJHIVIEXVZFX-UHFFFAOYSA-N 0.000 description 1
- UXGNAFUPNZUQQX-UHFFFAOYSA-N phosphanylmethylphosphane Chemical compound PCP UXGNAFUPNZUQQX-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5013—Acyclic unsaturated phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
- C07F9/5414—Acyclic saturated phosphonium compounds substituted by B, Si, P or a metal
- C07F9/5421—Acyclic saturated phosphonium compounds substituted by B, Si, P or a metal substituted by a phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/011,238 US4298541A (en) | 1979-02-12 | 1979-02-12 | Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts |
US4354879A | 1979-05-29 | 1979-05-29 | |
US06/114,627 US4302401A (en) | 1980-01-23 | 1980-01-23 | Tetraalkyl phosphonium substituted phosphine and amine transition metal complexes |
Publications (2)
Publication Number | Publication Date |
---|---|
SE8007080L SE8007080L (sv) | 1980-10-09 |
SE439439B true SE439439B (sv) | 1985-06-17 |
Family
ID=27359388
Family Applications (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8007079A SE8007079L (sv) | 1979-02-12 | 1980-10-09 | Fosfin- och fosfoniumforeningar och katalysatorer |
SE8007080A SE439439B (sv) | 1979-02-12 | 1980-10-09 | Katalysator och hydroformyleringsforfarande |
SE8007140A SE449093B (sv) | 1979-02-12 | 1980-10-10 | Kontinuerligt forfarande for framstellning av aldehyder |
SE8007139A SE449750B (sv) | 1979-02-12 | 1980-10-10 | Forfarande for hydroformylering och overgangsmetallkomplex for genomforande av forfarandet |
SE8200371A SE8200371L (sv) | 1979-02-12 | 1982-01-22 | Metallkomplex |
SE8204443A SE8204443D0 (sv) | 1979-02-12 | 1982-07-23 | Hydroformyleringsforfarande |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8007079A SE8007079L (sv) | 1979-02-12 | 1980-10-09 | Fosfin- och fosfoniumforeningar och katalysatorer |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8007140A SE449093B (sv) | 1979-02-12 | 1980-10-10 | Kontinuerligt forfarande for framstellning av aldehyder |
SE8007139A SE449750B (sv) | 1979-02-12 | 1980-10-10 | Forfarande for hydroformylering och overgangsmetallkomplex for genomforande av forfarandet |
SE8200371A SE8200371L (sv) | 1979-02-12 | 1982-01-22 | Metallkomplex |
SE8204443A SE8204443D0 (sv) | 1979-02-12 | 1982-07-23 | Hydroformyleringsforfarande |
Country Status (8)
Country | Link |
---|---|
EP (6) | EP0159460A1 (fr) |
JP (3) | JPS56500167A (fr) |
BR (3) | BR8006681A (fr) |
DE (4) | DE3034353A1 (fr) |
GB (3) | GB2057906B (fr) |
NL (4) | NL8020079A (fr) |
SE (6) | SE8007079L (fr) |
WO (4) | WO1980001689A1 (fr) |
Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4450299A (en) * | 1980-10-01 | 1984-05-22 | Exxon Research And Engineering Co. | Homogeneous hydroformylation catalysis with silyl substituted alkyl diaryl phosphine metal complexes |
US4440634A (en) * | 1981-08-03 | 1984-04-03 | Exxon Research And Engineering Co. | Organic salt compositions in extraction processes |
US4429161A (en) * | 1981-08-17 | 1984-01-31 | Union Carbide Corporation | Process for preparing organic tertiary polyphosphine monooxides |
US4522933A (en) * | 1981-08-17 | 1985-06-11 | Union Carbide Corporation | Hydroformylation catalyst containing bisphosphine monooxide ligands |
US4491675A (en) * | 1981-08-17 | 1985-01-01 | Union Carbide Corporation | Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands |
US4400548A (en) * | 1981-08-17 | 1983-08-23 | Union Carbide Corporation | Hydroformylation process using bisphosphine monooxide ligands |
US4593011A (en) * | 1981-08-17 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands |
DE3264581D1 (en) * | 1981-10-28 | 1985-08-08 | Monsanto Co | Synthesis of isoprene from linear butenes |
DE3365327D1 (en) * | 1982-10-21 | 1986-09-18 | Texaco Development Corp | Method for the preparation of alcohols and aldehydes by reacting olefins with carbon monoxide and hydrogen |
US5110990A (en) * | 1984-03-30 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for recovery of phosphorus ligand from vaporized aldehyde |
US4608444A (en) * | 1984-04-05 | 1986-08-26 | The Halcon Sd Group, Inc. | Process and accompanying catalysts for the hydroformylation of formaldehyde to glycol-aldehyde |
CA1237728A (fr) * | 1984-07-20 | 1988-06-07 | Anthony G. Abatjoglou | Preparation d'acides carboxyliques a partir d'alcools en presence de catalyseurs a base de complexe de rhodium |
US4927967A (en) * | 1984-07-20 | 1990-05-22 | Union Carbide Chemicals And Plastics Company Inc. | Production of carboxylic acids from organic formate esters using rhodium complex catalysts |
CA1248549A (fr) * | 1984-08-16 | 1989-01-10 | Richard W. Wegman | Preparation d'acides carboxyliques anhydres a partir d'alcools en presence de catalyseurs a base de complexe de rhodium, et d'une source d'ester organique |
US4593127A (en) * | 1985-01-11 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process |
US4633021A (en) * | 1985-11-29 | 1986-12-30 | National Distillers And Chemical Corporation | Olefin hydroformylation |
DE3546123A1 (de) * | 1985-12-24 | 1987-06-25 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
GB8614910D0 (en) * | 1986-06-19 | 1986-07-23 | British Petroleum Co Plc | Preparation of ketones |
EP0320546A1 (fr) * | 1987-12-15 | 1989-06-21 | Council of Scientific and Industrial Research | Catalyseur d'hydrogénation |
US4948870A (en) * | 1988-05-27 | 1990-08-14 | Shell Oil Company | Polymerization process |
US5001274A (en) * | 1989-06-23 | 1991-03-19 | Union Carbide Chemicals And Plastics Company Inc. | Hydroformylation process |
JPH0520984U (ja) * | 1991-03-04 | 1993-03-19 | 日本フルハーフ株式会社 | 貨物自動車における煽 |
IT1256601B (it) * | 1992-10-16 | 1995-12-12 | Eniricerche Spa | Composizioni supportate a base di tungsteno o molibdeno,procedimento per il loro ottenimento e proprieta' come catalizzatori eterogenei di ossidazione |
DE4242723A1 (de) * | 1992-12-17 | 1994-06-23 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden |
DE4431528A1 (de) * | 1994-09-03 | 1996-03-07 | Basf Ag | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
DE19617178A1 (de) * | 1995-05-04 | 1996-11-07 | Basf Ag | Verfahren zur Herstellung von höheren Aldehyden |
FR2743010B1 (fr) * | 1995-12-29 | 1998-02-20 | Rhone Poulenc Fibres | Procede de preparation par hydrogenation de catalyseurs a base de metal de transition et de phosphine |
ES2253552T3 (es) * | 2001-03-29 | 2006-06-01 | Basf Aktiengesellschaft | Ligandos para complejos de quelato de pnicogeno con un metal del grupo viii secundario y empleo de los complejos como catalizadores para la hidroformilacion, la carbonilacion, la hidrocianacion o la hidrogenacion. |
AU2002324067A1 (en) * | 2001-08-24 | 2003-03-10 | Basf Aktiengesellschaft | Method for the production of 2-propylheptanol and hydroformylating catalysts and the further use thereof for carbonylation, hydrocyanation and hydrogenation |
DE10355066A1 (de) | 2003-11-25 | 2005-06-23 | Basf Ag | Verfahren zur asymmetrischen Synthese |
KR101141634B1 (ko) * | 2004-07-20 | 2012-05-04 | 엘지전자 주식회사 | 세탁장치 |
US7294745B2 (en) | 2004-12-30 | 2007-11-13 | Council Of Scientific And Industrial Research | Process for preparing aldol derivatives from alkenes using catalyst |
CN101094826B (zh) * | 2004-12-31 | 2011-02-09 | 科学与工业研究委员会 | 使用催化剂从烯烃制备羟醛衍生物的方法 |
FR2894251B1 (fr) * | 2005-12-05 | 2008-01-04 | Air Liquide | Procede de synthese de methanol permettant un recyclage du gaz residuaire |
US9251837B2 (en) | 2012-04-25 | 2016-02-02 | Seagate Technology Llc | HAMR NFT materials with improved thermal stability |
US9224416B2 (en) | 2012-04-24 | 2015-12-29 | Seagate Technology Llc | Near field transducers including nitride materials |
US8427925B2 (en) | 2010-02-23 | 2013-04-23 | Seagate Technology Llc | HAMR NFT materials with improved thermal stability |
DE102011081074A1 (de) * | 2011-08-17 | 2013-02-21 | Areva Np Gmbh | Verfahren zur Herstellung eines Uranoxid als aktive Komponente enthaltenden Katalysators |
KR101611113B1 (ko) | 2011-12-20 | 2016-04-08 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포밀화 방법 |
US20140376351A1 (en) | 2013-06-24 | 2014-12-25 | Seagate Technology Llc | Materials for near field transducers and near field transducers containing same |
US9245573B2 (en) | 2013-06-24 | 2016-01-26 | Seagate Technology Llc | Methods of forming materials for at least a portion of a NFT and NFTs formed using the same |
US9058824B2 (en) | 2013-06-24 | 2015-06-16 | Seagate Technology Llc | Devices including a gas barrier layer |
US8976634B2 (en) | 2013-06-24 | 2015-03-10 | Seagate Technology Llc | Devices including at least one intermixing layer |
US9570098B2 (en) | 2013-12-06 | 2017-02-14 | Seagate Technology Llc | Methods of forming near field transducers and near field transducers formed thereby |
US9697856B2 (en) | 2013-12-06 | 2017-07-04 | Seagate Techology LLC | Methods of forming near field transducers and near field transducers formed thereby |
BR112016013001B1 (pt) | 2013-12-19 | 2020-12-29 | Dow Technology Investments Llc | processo de hidroformilação |
DE102014201122A1 (de) * | 2014-01-22 | 2015-07-23 | Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock (Likat) | Verfahren zur katalytischen Herstellung von ungesättigten Aldehyden |
US9620150B2 (en) | 2014-11-11 | 2017-04-11 | Seagate Technology Llc | Devices including an amorphous gas barrier layer |
US9552833B2 (en) | 2014-11-11 | 2017-01-24 | Seagate Technology Llc | Devices including a multilayer gas barrier layer |
US9822444B2 (en) | 2014-11-11 | 2017-11-21 | Seagate Technology Llc | Near-field transducer having secondary atom higher concentration at bottom of the peg |
US10510364B2 (en) | 2014-11-12 | 2019-12-17 | Seagate Technology Llc | Devices including a near field transducer (NFT) with nanoparticles |
TWI788364B (zh) | 2017-06-23 | 2023-01-01 | 美商陶氏科技投資有限公司 | 氫甲醯化反應製程 |
CN110975941B (zh) * | 2019-12-17 | 2022-08-05 | 万华化学集团股份有限公司 | 一种氢甲酰化反应催化剂组合物及丙烯氢甲酰化反应制备醛的方法 |
WO2022025562A1 (fr) | 2020-07-30 | 2022-02-03 | 주식회사 엘지화학 | Procédé d'hydroformylation |
JP2024500349A (ja) | 2020-12-22 | 2024-01-09 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化反応方法 |
US11980875B2 (en) | 2022-08-23 | 2024-05-14 | King Fahd University Of Petroleum And Minerals | Method for making magnetic nanoparticle supported catalysts |
GB202404300D0 (en) | 2024-03-26 | 2024-05-08 | Johnson Matthey Davy Technologies Ltd | Process for the production of 2-alkylalkanol |
Family Cites Families (54)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US644446A (en) * | 1899-04-07 | 1900-02-27 | Albert F Norris | Piano-pedal support and bearing. |
GB859391A (en) * | 1958-03-14 | 1961-01-25 | Ici Ltd | New aliphatic organic diphosphines |
US3239566A (en) * | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
DE1160855B (de) * | 1961-11-08 | 1964-01-09 | Bayer Ag | Verfahren zur Herstellung von Propargylphosphoniumhalogeniden |
US3857900A (en) * | 1965-12-15 | 1974-12-31 | Ethyl Corp | Hydrogenation of aldehydes using triarylphosphine rhodium halogenoid catalysts |
GB1189441A (en) * | 1966-03-21 | 1970-04-29 | Albright & Wilson Mfg Ltd | Organic Compositions containing Oxidation Retarders |
US3511880A (en) * | 1966-09-16 | 1970-05-12 | Union Oil Co | Hydrocarbonylation process |
US3487112A (en) * | 1967-04-27 | 1969-12-30 | Monsanto Co | Vapor phase hydroformylation process |
US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
US3954877A (en) * | 1967-10-12 | 1976-05-04 | Jefferson Chemical Co., Inc. | Hydroformylation of olefins |
US3547964A (en) * | 1968-07-24 | 1970-12-15 | Union Oil Co | Group viii noble metal catalyst recovery |
GB1298331A (en) * | 1968-08-02 | 1972-11-29 | Johnson Matthey Co Ltd | Improved hydroformylation process |
FR2041776A1 (en) * | 1969-05-30 | 1971-02-05 | Inst Francais Du Petrole | Novel rhodium contg hydroformylation - catalysts |
US3847997A (en) * | 1969-06-12 | 1974-11-12 | Phillips Petroleum Co | Hydroformylation process and catalyst |
US3729498A (en) * | 1969-09-24 | 1973-04-24 | Kurashiki Rayon Co | Process for the preparation of organic dinitriles |
US3832404A (en) * | 1969-12-19 | 1974-08-27 | British Petroleum Co | Hydroformylation process |
GB1342876A (en) * | 1969-12-19 | 1974-01-03 | British Petroleum Co | Catalyst supports and transition metal catalysts supported thereon |
US3657298A (en) * | 1970-01-06 | 1972-04-18 | Pressure Chemical Co | Arsenic and phosphorus containing polydentates |
US3859359A (en) * | 1970-04-27 | 1975-01-07 | Ethyl Corp | Compound and method |
US3821311A (en) * | 1970-05-21 | 1974-06-28 | Celanese Corp | Production of aldehydes from olefins |
DE2026163A1 (de) * | 1970-05-29 | 1971-12-09 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Aldehyden und/oder Alkoholen nach dem Oxoverfahren |
US3907923A (en) * | 1970-06-25 | 1975-09-23 | Atlantic Richfield Co | Oligomerization process |
US4098727A (en) * | 1970-07-23 | 1978-07-04 | Mobil Oil Corporation | Insoluble polymers having functional groups containing chemically bonded Group VIII metal |
US4072720A (en) * | 1971-01-19 | 1978-02-07 | Mobil Oil Corporation | Production of alcohol |
SU370212A1 (ru) * | 1971-02-01 | 1973-02-15 | Способ получения третичных арилэтинилфосфинов | |
US4179401A (en) * | 1971-07-08 | 1979-12-18 | Garnett John L | Preparation of heterogeneous catalysts including the steps of radiation grafting of an alpha unsaturated monomer to a metal or to an organic polymer |
GB1372189A (en) * | 1971-10-01 | 1974-10-30 | British Petroleum Co | Hydrogenating usaturated compounds |
US3939188A (en) * | 1972-03-24 | 1976-02-17 | Exxon Research And Engineering Company | Preparation of zerovalent phosphine substituted rhodium compounds and their use in the selective carbonylation of olefins |
US3987009A (en) * | 1972-06-15 | 1976-10-19 | Union Carbide Corporation | Transition metal catalyst compositions |
US3907852A (en) * | 1972-06-23 | 1975-09-23 | Exxon Research Engineering Co | Silylhydrocarbyl phosphines and related compounds |
GB1448826A (en) * | 1973-02-07 | 1976-09-08 | Dow Corning Ltd | Rhodium complexes containing sulphur and use as catalysts |
US4107079A (en) * | 1973-09-10 | 1978-08-15 | Rhone-Poulenc Industries | Insoluble metallic complexes and catalysts therefrom |
US3852328A (en) * | 1973-09-26 | 1974-12-03 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to a linear pentenenitrile |
US3929849A (en) * | 1973-10-01 | 1975-12-30 | Exxon Research Engineering Co | Tetraalkyl phosphonium aluminosilicates |
US4053493A (en) * | 1973-10-01 | 1977-10-11 | Exxon Research & Engineering Co. | Layered tetraalkyl phosphonium clays |
US4008281A (en) * | 1973-12-03 | 1977-02-15 | Monsanto Company | Asymmetric catalysis |
US3948965A (en) * | 1974-07-12 | 1976-04-06 | Union Carbide Corporation | Catalytic process for polyhydric alcohols and derivatives |
US4119652A (en) * | 1974-08-29 | 1978-10-10 | Monsanto Company | Catalytic asymmetric hydrogenation |
HU177239B (hu) * | 1974-10-15 | 1981-08-28 | Monsanto Co | Eljárás N-acetamido-L-alanin-származékok előállítására α-acetamido-akrilsav-származékok aszimmetrikus katalitikus hídrogénezésével |
US4013700A (en) * | 1974-11-25 | 1977-03-22 | Union Carbide Corporation | Catalytic process for polyhydric alcohols and derivatives |
US4052461A (en) * | 1975-02-03 | 1977-10-04 | Monsanto Company | Hydroformylation process |
US4157313A (en) * | 1975-02-26 | 1979-06-05 | Agence Nationale De Valorisation De La Recherche | Composite support notably for supporting catalysts containing a metal |
US4089890A (en) * | 1975-05-09 | 1978-05-16 | Imperial Chemical Industries Limited | Process for the dimerization of acrylonitrile |
US3954821A (en) * | 1975-06-30 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Carbon dioxide complexes of Rh, Ir, Ni, Pd, and Pt |
US4136103A (en) * | 1975-12-29 | 1979-01-23 | Exxon Research & Engineering Co. | Substituted tetraalkyl phosphonium aluminosilicates |
US4193943A (en) * | 1976-01-19 | 1980-03-18 | Celanese Corporation | Hydroformylation catalysts |
US4138420A (en) * | 1976-01-19 | 1979-02-06 | Celanese Corporation | Hydroformylation catalysts |
US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
US4089881A (en) * | 1976-11-12 | 1978-05-16 | Vanderbilt University | Complexes of metallated coordination ligands |
US4144191A (en) * | 1977-06-06 | 1979-03-13 | The Dow Chemical Company | Amine-resin supported rhodium-cobalt carbonyl bimetallic clusters as novel hydroformylation catalysts |
US4152344A (en) * | 1977-08-08 | 1979-05-01 | Celanese Corporation | Phosphino-ferrocene ligands |
US4201714A (en) * | 1977-08-19 | 1980-05-06 | Celanese Corporation | Stabilized catalyst complex of rhodium metal, bidentate ligand and monodentate ligand |
US4169861A (en) * | 1977-08-19 | 1979-10-02 | Celanese Corporation | Hydroformylation process |
US4179403A (en) * | 1977-12-19 | 1979-12-18 | Shell Oil Company | Resin-ligand-metal complex compositions |
-
1980
- 1980-02-12 DE DE803034353T patent/DE3034353A1/de not_active Withdrawn
- 1980-02-12 NL NL8020079A patent/NL8020079A/nl not_active Application Discontinuation
- 1980-02-12 WO PCT/US1980/000212 patent/WO1980001689A1/fr active IP Right Grant
- 1980-02-12 JP JP50065180A patent/JPS56500167A/ja active Pending
- 1980-02-12 BR BR8006681A patent/BR8006681A/pt unknown
- 1980-02-12 WO PCT/US1980/000213 patent/WO1980001690A1/fr active IP Right Grant
- 1980-02-12 BR BR8006679A patent/BR8006679A/pt unknown
- 1980-02-12 DE DE803034352T patent/DE3034352A1/de not_active Withdrawn
- 1980-02-12 EP EP85100028A patent/EP0159460A1/fr not_active Withdrawn
- 1980-02-12 NL NL8020088A patent/NL8020088A/nl not_active Application Discontinuation
- 1980-02-12 WO PCT/US1980/000215 patent/WO1980001692A1/fr active IP Right Grant
- 1980-02-12 BR BR8006680A patent/BR8006680A/pt unknown
- 1980-02-12 GB GB8031135A patent/GB2057906B/en not_active Expired
- 1980-02-12 GB GB8031137A patent/GB2056989B/en not_active Expired
- 1980-02-12 EP EP82107978A patent/EP0071281B1/fr not_active Expired
- 1980-02-12 NL NL8020087A patent/NL8020087A/nl not_active Application Discontinuation
- 1980-02-12 DE DE803034354T patent/DE3034354A1/de not_active Ceased
- 1980-02-12 JP JP50065080A patent/JPS55501178A/ja active Pending
- 1980-02-12 WO PCT/US1980/000216 patent/WO1980001691A1/fr active Application Filing
- 1980-02-12 JP JP55500652A patent/JPS6332079B2/ja not_active Expired
- 1980-02-12 GB GB8031136A patent/GB2086906B/en not_active Expired
- 1980-02-12 NL NL8020086A patent/NL8020086A/nl not_active Application Discontinuation
- 1980-02-12 DE DE803034351T patent/DE3034351A1/de not_active Ceased
- 1980-08-25 EP EP80900540A patent/EP0024091B1/fr not_active Expired
- 1980-08-25 EP EP80900539A patent/EP0023923B1/fr not_active Expired
- 1980-08-25 EP EP80900484A patent/EP0024088A1/fr not_active Withdrawn
- 1980-08-25 EP EP80900541A patent/EP0023924B1/fr not_active Expired
- 1980-10-09 SE SE8007079A patent/SE8007079L/xx not_active Application Discontinuation
- 1980-10-09 SE SE8007080A patent/SE439439B/sv not_active IP Right Cessation
- 1980-10-10 SE SE8007140A patent/SE449093B/sv not_active IP Right Cessation
- 1980-10-10 SE SE8007139A patent/SE449750B/sv not_active IP Right Cessation
-
1982
- 1982-01-22 SE SE8200371A patent/SE8200371L/xx not_active Application Discontinuation
- 1982-07-23 SE SE8204443A patent/SE8204443D0/xx not_active Application Discontinuation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SE439439B (sv) | Katalysator och hydroformyleringsforfarande | |
CN101200476B (zh) | 用于过渡金属催化的加氢甲酰化的双亚磷酸酯配体 | |
RU2422452C2 (ru) | Тетрафосфорные лиганды для каталитического гидроформилирования и родственных реакций | |
SU1715202A3 (ru) | Способ получени С @ - С @ -альдегидов | |
Kyba et al. | A facile synthesis of 1, 2-bis (phosphino) benzene and related alkylated species | |
US4960949A (en) | Low pressure rhodium catalyzed hydroformylation of olefins | |
PL152601B1 (en) | Transition metal complex catalyzed processes | |
EP2516373B2 (fr) | Réglage du rapport aldéhyde normal:aldéhyde iso dans un procédé d'hydroformylation à ligand mixte | |
JP7130624B2 (ja) | 高n/iso比アルデヒド生成物の調製のための安定なヒドロホルミル化触媒 | |
US4687874A (en) | Selective hydroformylation process using alkyl diaryl phosphine rhodium carbonyl hydride catalysts | |
CA2784943C (fr) | Reglage du rapport aldehyde normal:aldehyde iso dans un procede d'hydroformylation a ligand mixte par reglage de la pression partielle de gaz de synthese | |
NO172494B (no) | Bis-fosfitt-ligander | |
MXPA06010565A (es) | Metodo para hidroformilar olefinas en la presencia de compuestos organofosforicos. | |
US5648554A (en) | Method for producing aldehydes | |
AU759924B2 (en) | Hydroformylation process using chlorophosphite-metal catalyst system | |
US4450299A (en) | Homogeneous hydroformylation catalysis with silyl substituted alkyl diaryl phosphine metal complexes | |
CA2124525C (fr) | Procede d'hydroformylation faisant appel a un nouveau systeme catalytique phosphine-rhodium | |
US4668809A (en) | Transition metal complex catalysts | |
US4595753A (en) | Heterocycle-substituted alkyl diaryl phosphine rhodium caronyl hydride complex hydroformylation catalyst compositions | |
US5672766A (en) | Method for producing aldehydes | |
US4687866A (en) | Ligand exchange process for producing alkyl diaryl phosphine rhodium carbonyl hydrides | |
EP0054986A1 (fr) | Procédé d'hydroformylation d'oléfines | |
WO2000002890A1 (fr) | Procede d'hydroformylation | |
US4593141A (en) | Hydroformylation catalysis by branched alkyl diaryl phosphine rhodium complexes | |
US4408078A (en) | Process for the hydroformylation of olefins |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
NUG | Patent has lapsed |
Ref document number: 8007080-8 Effective date: 19900215 Format of ref document f/p: F |